Sideways (2004)

By Afra Nariman

Sideways (2004)

Directed by: Alexander Payne
Stars: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh

Plot Summary

Two friends, Miles and Jack (played by Giamatti and Church), take a road trip to wine country in celebration of Jack’s upcoming wedding later that week. Miles, a struggling writer and huge wine enthusiast, is recently divorced and prefers to spend the week relaxing and enjoying new wines with his friend. On the other hand, Jack, a somewhat “has-been” actor, is looking to find a week-long fling before he officially ties the knot with his fiancé, Christine. They meet a couple friends who share Miles’ love for wine, in Stephanie and Maya. Jack and Stephanie immediately hit it off and begin to sleep together, while Miles and Maya begin to develop a deep connection as they realize they have a lot in common. As the week goes on and Miles falls for Maya more and more, it becomes harder and harder for him to keep Jack’s secret from her and he eventually slips up.


On paper, this movie is about two friends who spend the week before one of them gets married, bonding with a couple of women who they meet while on a wine tasting trip. In its entirety, Sideways is about two men, mainly Miles, who finds himself while on a wine tasting trip with his friend. Coming off a divorce and constant denial from publishing companies for his book; Miles is lost, unsure of himself and his future. Slightly depressed, and not-so-slightly sadistic, he isn’t expecting much from the trip other than getting to spend time with his old friend. Surprisingly to him, after grudgingly agreeing to accompany Jack on a double-date so that Jack can have his last fling, Miles meets his perfect woman in Maya, who is fun, compassionate, intelligent and most importantly a fellow wine enthusiast. She breathes life back into the broken, dispassionate body and mind of Miles.

Sideways is one of the most raw, humane and relatable films I’ve had the pleasure of watching. Based on a novel, this movie has some of the most well-constructed and well-developed characters of any film. Each character, although we only get to know them over the course of a few days, has a deep and long history. We come to know and understand the characters, their history, their values and much more in a short amount of time. Additionally, the dialogue is full of substance and comes naturally throughout the film. One of the most rememberable scenes of the film comes from a conversation of wine between Miles and Maya. While explaining why he loves Pinot Noir so much, Miles seems to express his passion for the wine by personifying it and perhaps relating to the grape juice himself. He poetically says:

"It's uh, it's thin-skinned, temperamental, ripens early. It's, you know, it's not a survivor like Cabernet, which can just grow anywhere and uh, thrive even when it's neglected. No, Pinot needs constant care and attention. You know? And in fact it can only grow in these really specific, little, tucked away corners of the world. And, and only the most patient and nurturing of growers can do it, really. Only somebody who really takes the time to understand Pinot's potential can then coax it into its fullest expression. Then, I mean, oh its flavors, they're just the most haunting and brilliant and thrilling and subtle and... ancient on the planet."

In a way, Miles is giving Pinot Noir the humanistic quality of being an underdog, being sensitive, unique, and delicate. Knowing that he is dealing with frustration and is in pain due to his struggling career as a writer and failed marriage, its easy to see the emotion that Miles is speaking through, even when speaking about his favorite wine. He follows his poetic description of Pinot Noir by asking Maya why she loves wine so much. Maya also responds in a poetic manner:

" I like to think about what was going on the year the grapes were growing; how the sun was shining; if it rained. I like to think about all the people who tended and picked the grapes. And if it's an old wine, how many of them must be dead by now. I like how wine continues to evolve, like if I opened a bottle of wine today it would taste different than if I'd opened it on any other day, because a bottle of wine is actually alive. And it's constantly evolving and gaining complexity. That is, until it peaks, like your '61. And then it begins its steady, inevitable decline."

Both Miles and Maya talk about wine by humanizing it; making wine feel alive. This moment in the film, regarding this conversation, felt alive in itself. Wine definitely is an aspect of the film that has its own life; it breathes life into the story wherever its needed. In many ways, Sideways is a love letter to wine as much as it is an exploration of love itself and how love can overcome grief. The film also depicts a notion of morality in Jack’s character, as being void of morality. Often times throughout the film, Miles acts as the moral compass who combats Jack’s shortcomings in that area. Jack spends the entirety of the film chasing a fling during the week leading up to his wedding with Christine. Miles continuously expresses his disapproval of Jack’s behavior and at the end of the film, Jack admits that he has made a mistake and claims that he’s a bad person, bringing his character’s struggle with morality to an end (at least for that week)… but not before getting repeatedly bashed in the face with a motorcycle helmet by Stephanie.

An ultimate “feel good” movie, Sideways does so much so well. As the story progresses, it slowly becomes more and more relatable and captivating through meaningful dialogue, complex and humanized characters, and raw, brilliant storytelling. With an overall fun and giddy vibe to it, and some comedy sprinkled in, Sideways is one of the best told films that explore love (and wine). The entire film felt like an easy-to-watch, yet at times memorably intimate tale of Miles’ search for revival through love. By the end of the film we not only find ourselves feeling as if we truly know who Miles is, but we also find ourselves rooting for him; rooting for him and Maya, who we’ve also come to understand on a deep level, to be together at the end.

Wine could have easily become too much of a focal point of the film, to the point where it could have dominated the entire plot, but it didn’t. It was used perfectly as a connecting theme of the story’s characters. Wine is the drink of love; and in this film wine brought everything together. Although not a movie strictly about wine, in it we get an eduction on wine, a poetic description of it’s value and a love story that grows out of a shared passion for wine. Sideways is arguably Alexander Payne’s best film, primarily because of it’s relatable characters found in Miles and Maya, and in other ways, in Jack and Stephanie. A perfectly balanced story about friendship, love, morality and wine, told in remarkably humane and comedic fashion.


Rating: 5 out of 4.

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